


How to Win Your Heart

by ReadWithDetermination



Category: Undertale (Video Game)
Genre: A Dumb Friend But a Good Friend, Awkward Crush, Awkward Tension, Bad Decisions, Bad Matchmaking, Crack, Dancing and Singing, Dare, Don't Try This At Home, Drunken Confessions, Drunken Shenanigans, Fluff and Crack, Fluff and Humor, Funny, Good Chara (Undertale), Humor, Inspired by Music, M/M, Matchmaking, Mild Language, Mutual Pining, Never Give the Blueberry Coffee, Reader Is Not in the Pairing, Reader is a good friend, Reader plays Wingman, Serenading, The Author Regrets Nothing, Underfell Sans (Undertale), Underfell Undyne, Underswap Alphys - Freeform, Underswap Sans (Undertale), Undertale Monsters on the Surface
Language: English
Status: Completed
Published: 2019-12-28
Updated: 2019-12-28
Packaged: 2021-02-26 06:52:54
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,141
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21999277
Author URL: https://archiveofourown.org/users/ReadWithDetermination/pseuds/ReadWithDetermination
Summary: "And what have we learned?""Never give the Blueberry coffee and booze on top of a dare.  It never leads to anything good.""I wouldn't say 'never'...but please, don't do that again."(Prompt in the Notes!  Challenge awaits!)
Relationships: CherryBerry, Sans/Sans (Undertale)
Comments: 11
Kudos: 42





	How to Win Your Heart

**Author's Note:**

> I had a bit of a rough week, so I tried to cheer myself up with some music. That's when this little gem popped into my head.  
> Crack at its finest!
> 
> Anyway, here's the prompt i devised if anyone wants to give it a go (RWD's Crime & Motive Prompt!). This story's was this:
> 
> Character: Reader  
> Crime: Disturbing the Peace  
> Motive: Matchmaking
> 
> The Prompt involves choosing any character, crime and motive, and writing a fic based around that. Have fun!!!
> 
> **THIS FIC IS DEDICATED TO ANYONE & EVERYONE THAT JUST NEEDS SOME NONSENSE IN THEIR LIVES**

You should have known hearing your friends yell "DO IT, NERD!" at the top of their lungs as moral support heralded disaster.

And you most certainly should have known better than to actually go along with it.

The problem was the love life of your good friend Sans was at stake and, by thunder, you were going to get the little fellow out of an emotional funk even if it killed you!

Which, considering the way the night was turning out, might not be too far from the case.

You did send your little buddy Frisk a text saying they might want to SAVE and in a hurry, considering you were about to do something really dumb. Chara was in your group and had already said they weren't reviving you if this failed. No, they were just smirking from the porch of Alphys' house. Blue's Alphys, not Red's Alphys. 

Ugh, why couldn't they agree to have nicknames the way the skeletons did? But no, the warrior fish and stab-happy lizard were too stubborn to agree on code names and, honestly? Their girlfriends were actually worse than they were when it got down to it. Years of defending OTP ships had given them a lot of practice, you supposed.

Speaking of OTPs...

You looked up at Blue who was bouncing around in one place so much you thought he might explode. Dammit, you were really regretting giving him that much coffee. You knew he was naturally energetic to the point any little energy-altering substance might be considered a catalyst for trouble, but you couldn't help yourself. His brother, Stretch, had also warned you before, but you'd wanted to see what damage could be done by giving him a hot chocolate.

Muffet was not amused, and you're still not sure exactly _how_ Blue managed to find all of those twinkling lights, nor how he managed to find enough to decorate the entire street. Still, he took them down later, and your neighbors - including that one very snooty couple - were pleasantly surprised to find out they had won the "Best Holiday Light Display" award. So, instead of calling the police over Blue's very strange vandalism, they were now lording their prize over the heads of another bunch of equally snooty jerks in the next community over.

Now, as you looked around at the objects you had acquired for this horrible night of frolic, you were questioning whether Frisk would be willing to help you after they learned what you did.

Currently, twenty radios of various shapes and sizes lined the backyard, with over half of them rigged with volume-enhancing gadgets created by Science Lizard and Geek Fish. All twenty of them were aimed at Red's bedroom. In the center, still bouncing around on his toes, was Blue, whose caffeine intake was due to hit at any moment.

Because if one hot chocolate could make him decorate the whole neighborhood, then who knew what an entire _pot_ of "Death Wish" was going to do?

Especially when Stabby Fish had already gotten a bit of chocolate liqueur into him.

God, Blue was a clingy drunk! Happy, huggy, and a little whiny, but once he latched on, it was like trying to pry a koala bear off an eucalyptus tree. When he'd done that to (his) Alphys earlier, it reminded you of a scene from a Halloween cartoon you once watched as a kid - one where some guy tried to interrupt a party and steal a girl's attention back from the new teacher in the area, only to have a very overzealous young lady leech herself onto him and start dancing around until he threw her into a closet.

...Come to think of it, Blue was probably about the same height as the lady in the cartoon, wasn't he?

When you thought about the scene possibly replaying itself with the flustered (and possibly homicidal) object of Blue's affections being in the place of ye olde Brom Bones (heh, _Bones_ ), you had to stifle a laugh.

And a twinge of horror.

"We're gonna get shot," you told Undyne (Stabby Undyne, not Science Undyne).

"No, we're not," she retorted with a gruff whisper before ruffling your hair. "We're gonna get stabbed!"

The fact that said this with such an insanely happy grin on her face made you start to question your choice in friends. Almost. Okay, not really - not when you were the ringleader in this horrible mess of an idea that had only maybe about a 1.3333333% (carry the 7) chance of working without anyone getting dusted and Blue finally getting his man.

Because that's why you'd helped drag twenty boomboxes out here in the middle of the night and dosed Blue up on the strongest coffee known to either man or monsterkind:

You were tired of him moping.

Seriously, _moping_! You weren't even aware the Blueberry could do that! And, oh, it did not suit him, at all! No, seeing the wide and cheerful grin on his face reduced to a mere shell of its former brilliance as he hmmed and sighed as he stared forlornly into his tea cup-

Yeah, your heart couldn't take it. You were one badass bitch (or bastard), but that? Nuh-uh. That face didn't just break your heart, it smashed it into tiny little pieces, crushed them under one of Mettaton's patent leather boots, yeeted them into a wood chipper, and then set the whole damn thing on fire before walking away, laughing like a maniac!

You may have even shed a tear yourself.

What wound up happening was (his) Alphys trying to shake the happy back into him the moment she walked into the cafe, and your having the girls huddle up. That the huddle then turned into a group hug of said little skel was par for the course.

You see, the problem was your little buddy was skull over his heels for his buddy Red. And Red just wasn't taking the hint.

Oh, it was the saddest case of two people being utterly oblivious to how much the other liked them that you'd ever seen! Not to mention Red's legendary self-worth issues. That boy had anxiety _in spades_. 

Any time Blue did something nice for Red, you could see Red's grin quirking up nervously, as if letting out any of his happy was going to signal the Apocalypse. He'd start twitching and sweating and find some reason to go hide from Blue - because _of course_ , one of them just HAD to be a self-denying basketcase, didn't he? Obviously, since Blue couldn't read minds, any time Red ran off like that, his feelings would get hurt, but he'd usually double-down later and try again with some new scheme since Red never said he didn't actually want the attention.

But one day, he'd managed to corner Red, and the Underfell monster's Mariana Trench-levels of low self-esteem had raised their ugly head and had countered Blue's finally asking him on a date with an "I CAN'T" loud enough for the entire city to hear before he teleported away. And it left the poor little Swap skeleton so soul-shattered he'd been ready to give up.

At this point, IF you managed to survive the night, you were dragging Red to therapy. The way he was so down on himself was just unhealthy!

So, after having a talk with Red just to make sure it really WAS his dirt-poor sense of self-worth getting in the way and his not actually wanting to get Blue to leave him alone (he didn't really, but he was in one of those "wah, wah, i don't deserve nothin'" moods of his and there wasn't any way to get him out of it), you decided on THIS:

The result? One very enthusiastic and inebriated skeleton performing a "grand display of the Great and Magnificent Sans' Romantic Intentions" toward another skeleton of the same name, whom was affectionately (or infamously, depending on your brand of humor) also known as Red. Complete with an entourage.

"You ready?" Undyne asked.

You looked back at the porch of the house next door and saw that the other Undyne and Scientist Alphys had joined Chara, with both monsters looking both eager and more than a little concerned. Then you looked at the hyper skeleton that both guard monsters had spent the past half-hour pep talking - and by that, you meant they were yelling encouragement and getting him to do War Cries in the living room.

 _Welp, time to get on with the rest of this drunken-hyper mating dance_ , you decided. 

Taking a deep breath, you nodded to the Alphys and Undyne with you, and the three of you donned the paper plate masks you made. You were almost glad you couldn't see the liquid glitter and sequences smeared all over the face, but one twitch of your head made the feathers sticking all around the sides make tiny whooshing noises.

"Let's do this," you said, which was loudly echoed by an unanimous "DO IT, NERD!" and whooping as the geeky fish, far away from the danger zone, lifted a remote and pushed a button.

...

...

...

What followed was the most glorious, most terrifying, and most insane convergence of sounds you had ever heard in your life. If fifty-four tomcats had all been yowling for their lady loves, it would have sounded more harmonious that the chaos that ensued.

In an instant, floodlights that had been strung up to extension cords from the house next door flooded on, leaving four figures - one standing proudly as his cape fluttered in the wind, and three others decked in sheets (yes, SHEETS, it was Stabby Fish's idea) and paper plate masks - looking incredibly ominous because of the angle of the light behind them left their figures drenched in shadow, as the most horrific mashup of every possible version of the same kid's song came roaring from the speakers of the boomboxes surrounding them.

You were very thankful you'd put in earplugs.

" _HEY, WITCH DOCTOR! GIVE US THE MAGIC WORDS!_ "

You felt your sins crawl up you back with those words before they scattered into the night. None of them wanted to stick around to witness this atrocity.

A comically deep voice boomed out across the yard, joined in by several more voices - all the same audio clip with the pitch edited - saying the "magic words".

Blue started hopping and cackling with glee as you and his other friends began psyching him up.

Then the screaming began.

It wasn't singing. 

No, no singing could EVER compare to the caterwauling that came out of all of you. You were all too hyped up (and, in your case, a bit scared) to care once you got started. The bass pounded, clearly rocking the windows of the residence in front of you. A glance over and you saw the bird feeder in the tree of the adjacent yard was swinging away from the vibrations. At one point, Fell Undyne yelled for her counterpart to pump up the volume, and you swore you heard a car alarm go off out front as the next round of "ooh ee ooh ah ah" sounded off.

For roughly the next minute, Blue belted out the words of the song just audible enough to be heard over the booming music, wobbling but somehow managing to stay upright despite his increased levels of intoxication, with you, Alphys, and Undyne waving your arms and belting out the chorus. A few times, Blue nearly tipped over and you had to grab his cape to steady him - allowing you to catch sight of a really weird look on his face and two heart-shaped eyelights that kept shifting sizes.

It was then in the midst of Blue doing whatever the heck his alcohol-and-coffee-addled brain was telling him to do in terms of choreography that you realized you'd forgotten one very important part of the equation-

-and then a pair of strong red eyelights flickered on angrily in the second-story window from Edge's room.

Oh, boy. That was NOT part of the plan.

You saw the taller of the two brothers throw open the window before being jarred back by the sheer intensity of the music. You couldn't hear what he was saying but, judging from the way he was snapping his mouth open and closed and covering where his ears should be (if he had ears), you could probably say he wasn't very happy. He stopped for a split second, his murderous glower perfectly illuminated by the floodlights, before turning to yell back into the house.

You caught sight of Red's groggy face appear in his own bedroom window, to which Blue - who was completely oblivious to Edge having ever noticed the chaotic performance, as he was far too focused on Red's room - commenced to waving and shouting grand exaltations of...something. Probably how much he was enamored with the baffled bag of bones at the window. You couldn't really tell.

However, you did notice that once Blue started gesturing toward the window and bouncing around with the most ecstatic expression you had ever seen on his face, Red's arms flew up and he disappeared back into the dark recesses of the room.

A few moments later, the back door flung open, and Edge tore out of the house, his brother in tow. Then Edge's eyelights flared and - oh, boy, those bone attacks couldn't mean anything good.

You didn't even have time to yell "Scatter!" before your friends took off every which way - except for Blue, who was in the middle of what looked to be a spin cycle. You were knocked off your feet by a fleeing Alphy's tail, only narrowly missing a bone as it sailed over your head. Within seconds, each of the radios died, speared to death by Edge's wrath.

Then, you yanked the plugs out of your ears just as Edge yanked Red up by the collar of his long nightshirt (who knew the brothers were partial to the long nightshirt-and-stocking-cap combo?) to yell in his face.

"THIS IS WHAT HAPPENS WHEN YOU DON'T TAKE CARE OF YOUR SHIT, SANS!" he yelled. 

Next thing you knew, Red was flying through the air, coming to a complete crash only after impacting with Blue. You glanced over, seeing Alphys vault over the fence of the porch and into the nearby house as the porch light winked out. 

_Freaking traitors_ , you thought. Leaving you and Blue to die like this. You thought guards had a policy of leaving no monster behind?!

Edge let out a harrumph, gaining your attention again.

"STOP PINING OVER BLUE AND GO ON A DAMN DATE WITH HIM ALREADY! NOW, CLEAN THIS MESS UP AND DON'T WAKE ME AGAIN!" 

...And into the house he disappeared, letting the screen door swing shut with a _bang!_ that shattered the silence that had now permeated the yard.

A split second later, you felt a hand grab at your back, wrenching into the sheet and shirt beneath it. "Time to go, human."

Suddenly, you were on the darkened porch of the house with the bird feeder. Blue and Stretch's house.

 _At least one of my friends came to my rescue_ , you thought. You turned around and looked up into the face of Stretch, who thankfully looked more amused than upset for your having woken him up. He looked over your head and regarded the remains of your insane attempt at matchmaking.

"So that's what you meant when you said you had a plan that might cheer Sans up," he said, the tired mirth in his voice barely restrained.

You looked back to the chaos. Blue and Red now sat in the yard, their figures partially lit by the awkwardly aimed floodlights and surrounded by smoking and sparking radios and gleaming white and red bones.

"Well, it was one way to get Blue to just out and confess to Red," you said, regarding Stretch again with a sheepish smile. "We just kinda hoped that maybe Red would finally get it if he saw we were all supporting them both."

Stretch raised a brow ridge. "By playing 'The Witch Doctor Song' in the middle of the night so loud you set off Blue's car alarm?"

You _thought_ you heard a car alarm go off! Stretch chuckled.

"It was so tiring watching the two of them pine over one another and Blue getting sorta-rejected time and again because Red couldn't get the picture that it was okay for him to have feelings!" you puffed up, crossing your arms over your chest in a way that admittedly was a bit childish. "I just wanted to help."

Stretch, now looking past you again, said, "I don't think you have to worry about Red getting the picture anymore." He then nodded toward the scene in the yard.

You turned around just in time to see Red rub the back of his skull while Blue's little heart eyes grew to nearly fill his eye sockets. A moment later, you heard Red say something inaudible and nod right before Blue let out a squee any fangirl would be proud of and literally tackled the other skeleton with a smooch that sent them both reeling to the ground.

There was no hiding your delighted gasp, and you were now bouncing almost as much as Blue was moments ago. 

"Happy?" Stretch asked. 

You turned and started nodding as fast as you could. 

"Well, that's good. Because I don't think the rest of the neighborhood is."

You gave him a puzzled look before turning around to see the flashing lights of a patrol car heading up the street. You whirled around on Stretch and grabbed the front of his hoodie. 

"Save me...!" you whisper-pleaded.

"Heh. Nope."

And then you were suddenly left holding air as the police officers pulled right up along the street.

You yanked your phone out of your pocket and frantically started texting.

' _Frisk! Kid! Save me so I don't have to ride in the back of the whee-whoo car! Frisk? Frisk, honey, LOAD! LOAD LOAD LOAD LOAD LOAD!!!_ '

...Frisk did not LOAD, and instead joined in with Chara the next day teasing you about how the cops had lectured you for a good thirty minutes and how you narrowly avoided getting charged with disturbing the peace.

"And what have we learned?" Stretch asked you sat on the porch stoop after the cops left, head in your hands. You could have sworn you heard distant laughter, and you weren't sure if it was Edge, your snooty neighbors, or your own exhausted imagination.

"Never give the Blueberry coffee and booze on top of a dare. It never leads to anything good."

"I wouldn't say 'never'...but please, don't do that again."

Still, seeing how happy your two skeletons buddies were now that they were finally together?

Absolutely _worth it_!

**Author's Note:**

> ...Yeah, I don't regret a damn thing in writing this. We needed some pure humorous fluff and crack after all the feels trips from BJC.  
> Also, added in UF!Undyne (and for a moment, UF!Alphys) because they can be misunderstood monsters who just want their pals to be happy, too.
> 
> Hope you got a giggle out of it!  
> Happy (early) New Year! ^-^

**Works inspired by this one:**

  * [Oop?](https://archiveofourown.org/works/22045306) by [dreamspiderdance](https://archiveofourown.org/users/dreamspiderdance/pseuds/dreamspiderdance)




End file.
